Inspiring Young Entrepreneurs | An Interview with Brian Weisfeld, Founder, The Startup Squad

entrepreneurial mindset entrepreneurship social entrepreneurship youth development youth entrepreneurship program Mar 22, 2023

Welcome to interviews with education leaders where Dr. Sonya Toledo connects with business professionals, thought leaders and social entrepreneurs to discuss how to make a difference in our education system. This interview is brought to you by Dignity of Children® where we are changing education one teacher, one parent, one student at a time. Join our vibrant professional learning community for forward thinking educators

(This interview was originally done as a video interview, you can watch the interview through the link HERE).

Hi, this is Sonia Toledo. I am the founder and CEO of Dignity of Children®. We're doing interviews with experts in education that are doing entrepreneurship programs and amazing work to support our young people develop the mindset of entrepreneurs. Today, I am interviewing Mr. Brian Weisfeld who is the founder of The Startup Squad. He created not only a series of books for young ladies, but he's also in a movement to show young people that they could be entrepreneurs from as young as kindergarten to 6th grade.

Dr. Sonia Toledo: Hi Brian, Welcome. Tell us what you've been doing.

Brian Weisfeld: Despite the fact that I'm in Silicon Valley right now, I'm a native New Yorker, I grew up on Long Island, I spent my whole adult life in New York City and I miss it terribly and try to get back to New York as much as I can. I've spent my career helping entrepreneurs scale and build their businesses. I was part of a three persons team that bought IMAX movie theater company in the early 90s and helped to turn that into the company that is today. Afterwards, I moved out here to be the Chief Operating Officer of and helped to grow that business. But as you said, I discovered my calling in inspiring girls and all kids to start being entrepreneurs at an early age.

Dr. Sonia Toledo: What was the spark? What was the event that had that spark happening?

Brian Weisfeld: Actually there were two separate events that came together to cause the spark. The first was, I've got two daughters who are now 16 and 14. When my older daughter was eight, she was in the Girl Scouts and she was selling cookies for the first time. Around the same time, she ended up doing a charity bake sale with a friend of hers. She was so excited to do it, but she didn't really know what to do. She was standing at the end of our driveway with all her boxes lined up, and she was just standing there and didn't know that she should say good morning to people when they walked by to get their attention and to look people in the eye when they talk to them and tell people that the money goes to charities. Even if they don't want to buy a brownie or a box of cookies, they could still help the cause. I didn't really think much of it, but as I was watching her I was realizing that these were life skills that she was learning how to talk to strangers. We always tell kids, don't talk to strangers, but ultimately, you got to learn how and to look people in the eye and to get comfortable with failure, and people say saying no and taking risks and all those wonderful things you learn just from a simple bake sale.

It didn't really hit me until about a month or so later. I was actually laying in bed reading books with my daughters on a Sunday morning, and I just got frustrated and tired of all of the Princess Rainbow Fairy Unicorn books that they get peddled to girls. I give those books a ton of credit because they help my daughter's imagination. They make her want to learn how to read. But why can't we do that at the same time that we empower girls and lift them up? And for whatever reason, at that exact moment, laying in bed on a Sunday morning reading books with my daughters, those two experiences combined in my brain, and I said, I'm going to create this movement to get girls interested in opening up that first Lemonade standard bake sales so they can start to think like entrepreneurs.

Dr. Sonia Toledo: This is so exciting. Of course I'm a girl, and I'm an entrepreneur, and I want as young as possible to get that spark to say, yeah, I could do this. I would love to learn a bit more specifically about the life skills that the Startup Squad will support in creating in young girls.

Brian Weisfeld: Our mission isn't that every girl should grow up to be an entrepreneur. I mean, if that's what they want to do, then great. But we just feel so strongly that the things that you learn from entrepreneurship, obviously, learning how to take risks, learning how to fail, learning that it's okay to fail, and that you learn something from it. I travel the country doing in-person, and I also do virtual school visits and library visits and talk to Girl Scout troops all across the country. One of the things I tell them is that entrepreneurs are comfortable taking risks and they're comfortable failing because they know that even if they fail, they're going to learn something that's going to help them succeed the next time. What I say is, entrepreneurs don't say win some, lose some. They say, win some, learn some and I sort of make that point over and over again. I want girls to see opportunities instead of problems. I want them to say yes when everyone else is saying no. All those amazing things you get from that, developing that entrepreneurial mindset.

Dr. Sonia Toledo: I love that you say that win some, learn some. I grew up in a culture where failure had you stop and instead of feeling that I could learn something from this failure or this challenge that I'm coming across, it's almost like I don't know how. So I just won't do it. So let's talk a little bit about how important this skill concept is for our education in general, for girls and boys.

Brian Weisfeld: Look, we all fail in life. It just happens. Not being afraid to take that risk and realizing that it's okay to fail, if you can develop that skill as a kid, that's going to make you a much more powerful and much more successful adult. I also try to try to destigmatize failure. When I talk to kids, I tell them that when Beyoncé was nine, she was on a TV show, Star Search, it's like America's Got Talent for kids, and she lost. Can you imagine Beyoncé lost at a talent show when she was nine? But she didn't say, well, I guess I'll go become a chef now, rather she used that as motivation to keep working. So I tell kids the story of Beyoncé and of other famous people that fail because they look, and they look up at these people and they think that everything was so easy for them, and they don't hear the bumps in the road of the journey. It’s the bumps in the road of the journey that allow them to be that successful, to give them that motivation, to give them those learning experiences to be able to succeed. I think it's important that we realize that everyone experiences failure. I try to do it around my dinner table. It's something I learned from Sara Blakely, the founder of Spanx. She used to say that at her dinner table growing up, her father would ask her and her siblings, what did you fail at this week? and if they didn't have a good answer, he would be disappointed. So, I try to do that with my kids as well, not only to ask them what they failed about, but to share the things that I failed at so they realize that I'm still making mistakes and I'm still learning. I also tell parents all the time; share your failures, don't hide your failures. Make your kids realize you failed, but this is what you learned from it, and this is what you're going to do about it.

Dr. Sonia Toledo: Amazing. The entrepreneurship mindset in itself is amazing. So tell us Brian, what are some of the skills that are critical for our young people to learn, having this mindset?

Brian Weisfeld: There are studies that say that around 70% of the jobs that our kids are going to grow up to fill haven't been invented yet. So how do you train and grow a kid for a job that doesn't exist yet? Well, you train them to think, to be flexible, to be curious, to be comfortable taking risks and going into unknown situations. Also, the Sales skills, obviously are incredibly important no matter what you're doing. Being able to convince someone of your idea, your proposal, or whatever it happens to be. So developing those sales skills at a young age also is another incredibly valuable tool that you get from entrepreneurship.

Dr. Sonia Toledo: This is very interesting, you're coming up with these elements that we have created, like these negative feelings about like, oh, you're a salesy, you're a salesperson. So, sales skills, a real good salesperson doesn't sound salesy. Why is that?

Brian Weisfeld: I think it's not understanding necessarily what you're selling, but understanding the problem that it's solving for your customers. Everyone has problems, and so understanding the problem and what can solve it. One of the other things I do with kids is I show them if I'm in-person, I'll hold up a picture of a hammer or I'll hold up a hammer and I'll say, who can tell me what this is? And then the kids will raise their hand and I say, put your hand down if your answer is going to be a hammer, because the hammer is the name of it. It's not what it does, not what it is. So, what it is? This is a bizarre metal shaped object that usually has a handle you can grip onto. No one walks into a hardware store and says, hello, I was thinking do you have any weird metal shaped things that I could buy? They buy a hammer because of what it does, because of the solutions it provides for the problems they have. For example, I want to hang a picture, I want to build something, that's why you buy it. To be able to try to figure out what problem your product or your service can solve for someone is an incredibly valuable skill. You're interviewing for a job. What's the problem that they're trying to solve? How can you best help that person solve that problem? In school as well, when you're trying to make your arguments or convince a teacher of something, those same skills come in. So, it's not just coming up with a random sales pitch, but it's about trying to understand your customers and their problems.

Dr. Sonia Toledo: Awesome. I would like to quote Jim Ryan who once mentioned how being a salesperson is probably one of the most complex and most high level skills you could have in business across the board. Having sales skills is a very critical part of being in business or an employee, or just career wise. Like you said, when you know that what you're doing, what you're serving is supporting a problem, is solving a problem for someone, that's a skill that they're developing as they're learning how to create their business.

Brian Weisfeld: I would like to add that a lot of kids are shy. They're told not to talk to strangers, so they're not comfortable in coming up with and doing that. So what we talk to kids about is when you come up with a sales pitch, that's going to be something that you're going to say to everyone who walks by. If you're selling lemonade, it's hot out, would you like some cool, refreshing lemonade? And if you memorize a sales pitch like it's a line in a school play, all of a sudden, it takes a lot of the anxiety out of it for kids, because they're just saying the same thing to every person. It doesn't become as much of an anxiety provoking experience. That's one of the things we talk about. You find that kids coming out of their shell. I've worked with a lot of painfully shy kids but when they start doing that and they start coming with sales pitch and they start selling something and they see the reward when they're paid for it, that helps to bring them out of their shell. This has really done amazing things for a lot of girls that we've worked with.

Dr. Sonia Toledo: Awesome. I've had the same experience. I watch young people during our Youth Entrepreneurship competition. When they're in front of judges and experts, whatever question comes at them, they show up powerful, confident, and it's a wonderful thing to experience. So I love that we're talking about specific skills that help our young people develop to be our change makers but I also want to hear more about your books. I really can't wait to share these books with our network in New York City that really just want so many different avenues on how to relate these skills and help their staff transfer these skills into practice with our young people. So I'm looking forward because I had a chance to do some research and read the books. I want to hear from you. What was your thought process and how these books came alive?

Brian Weisfeld: So, once I had the moment of inspiration, I realized I wanted to do a fictional series. In my mind, a girl is going to pick up a nonfiction book about starting a business. She's already on the right path. So what I wanted is for girls and boys that had never thought about opening a business before to read a fun story about these four 6th grade girls who are running these businesses and say, hey, that sounds like fun. I want to do that, too. So, the books are fiction, but we divided them into three parts that I call the Inspiration, the Information and the aspiration. The inspiration is the novel. It's the story of these four 6th grade girls, and it's got everything that 6th grade girls deal with their family issues and friend issues and pets in school and all those things. But on the side, they're running businesses. But the book is very subtle in the way it discusses the businesses. It doesn't really hit you over the head that they're running a business. It just is a fun experience that they happen to be doing. The next section of the book in is the information section. We have a nonfiction section with actual business tips that kids can use and we refer back to the narrative. So we'll say, hey, remember when she made a big sign for her lemonade stand? Well, that's actually called marketing and here are some marketing tips you can use for your business. So we tie the nonfiction back to the fiction. The last part of the book is the aspiration. We have an interview with an actual girl CEO. This is a tween, or teen girl who's running a decent sized business. Because we want kids to realize that just because they're a kid, it doesn't mean they can't run a big business. So we do all those things but also, obviously, we're combining literacy with teaching entrepreneurship. We found out that a lot of programs that are teaching entrepreneurship are using our books to make the programs more effective. For example, the Girl Scouts. Obviously the Girl Scout cookies, the biggest fundraiser of the year, I've worked with a lot of Girl Scouts where the whole troop will read the book before a cookie selling season. And then either I or the troop leaders talk to the girls about the lessons in the book and relate it to cookie sales. We found that the girls are much more excited about selling cookies. They do a much better job, and they have a much better sense that they're not just selling cookies, they're actually running a small business. Those are some of the ways that we've done it and it's been just wonderful to see the reactions in each book has a different storyline, has different business tips in the back and an interview with a different girl entrepreneur.

Dr. Sonia Toledo: Awesome. First of all, it's really applying some skills that we do every day. Challenges come up. When you have a business or when you have an idea or you have a project that you want to produce, you're going to come across some challenges, which is part of everything that we do. So share with us some of the challenges that you have in starting your business, publishing the books and moving this forward into our education system.

Brian Weisfeld: Yeah, well, certainly a lot of challenges. I would say there are three challenges that come to my mind. First, I'm a business person, not a writer. So, I had to learn how to write. Not that I thought I'd be the person to write the books at the end of the day, but I knew I had to get down on paper what I was trying to create so I could test it with girls as beta readers, but also say to a publisher, look, this is what we're trying to do. So I spent three years learning how to write. I went to writing conferences, I took writing classes, I read. The first thing I did was I bought writing children's books for Dummies and I started reading there. I worked with freelance children's book editors, it was a three year process. We were to create that original manuscript which was obviously a massive challenge. I did a TEDx where I talked about some of the more entertaining parts of my journey in learning how to be a writer.

The second challenge was as a person who's sort of spent their career running businesses, I was always using the left side of my brain, if I have that right, and not using the creative and the right side of the brain. So, for the first time since I was a kid, sharing my own creative work was incredibly scary. For me, it was really just exposing a side of myself that I'd never exposed before. But at the same time, something I knew that wasn't nearly as developed. I knew how to run a business. I didn't know the first thing about writing, but I knew I had to share that creative side with people. So, that was obviously a very big, very big challenge.

The third and the last challenge is something that I've somewhat grown accustomed to. Each stage in my career, I've entered into a new industry. I think that I sometimes say the only common thread between each of the jobs I've had is I've never had any experience in that job before I started it. Similarly, here, I had to learn how the publishing industry works, that's part of it. I mean, you can write an amazing book, but if you don't know how the industry works and how to get a book published, it's going to be very hard for you to be successful. So that was another challenge in just sort of learning the ins and outs of the industry.

Dr. Sonia Toledo: That's awesome. The truth is that not only entrepreneurs, but anyone in their journey, it's about processing and learning new things that they have to learn in order to get the job done. You don't just get this in school, you actually have to live it to learn the process and learn that new skill. Tell me, what would you say is one of the key areas you would like to see different in our education system?

Brian Weisfeld: Obviously, given my role and what I've been doing, I would love to bring more entrepreneurship into the classroom. I think one a tremendous amount of fun, as well as a learning experience and a fundraising effort as well. I think we have a teacher's guide that goes with our first book, where we help teachers set up a program similar to the plot line of the first book, where in the first book, the kids are going on a field trip to the local amusement park, and all the kids get put into teams, and they have to run competing lemonade stands. So, to be able to do that, your classroom should be teaching the kids entrepreneurship, but also using it as a fundraiser for whatever the schools need funds for nowadays, which obviously is a substantial list, is a great way to do it. So integrating entrepreneurship in and there's a lot of organizations out there, such as Dignity of Children®, that are doing some amazing work. There's a group that works with kids in Appalachia, teaching them about entrepreneurship. And I actually went to a conference where they were educating teachers, and I met a Home Economics teacher and I was thinking what's a Home EC teacher doing here teaching economics or learning about entrepreneurship? And what she was doing was she was integrating entrepreneurship into a program. All the kids would bake something, they'd bake cookies, they'd learn how to do something, and then they actually sold it. She went out and she had the kids build a little cart, and they would drive the cart, they'd push the cart around the school, and that's how they would sell their cookies and things. So, she integrated entrepreneurship into her existing curriculum. So it doesn't have to be you've got math, science, English, and then you've got a period of entrepreneurship, instead you could integrate entrepreneurship into so many things. Obviously, from a math perspective, figuring out profit and loss of what you're doing, from an English perspective, coming up with a sales pitch and marketing pitch and those sorts of things, there's so many ways to do it. I think if you can get kids starting to develop that entrepreneurial mindset in addition to all the things that they're learning, they'll be much more successful.

Dr. Sonia Toledo: I love it, and it's also part of marketing and branding yourself. That's something that I've learned being in business is like, I got to brand myself and I got this haircut that everybody knows me about. It's part of my branding. But also I tend to giggle a lot or cry. It's one of my things that she's either going to cry or giggle. But the branding is also branding yourself and having integrity and showing up consistently to your audience and people who want to learn from you. So this is really exciting for me. Tell us how we could get a hold of your books, contact you, and get to know more about the work that you do and where you're located.

Brian Weisfeld: Sure. So the books are available wherever books are sold. We're a big fan of supporting your independent bookstores. You can obviously also buy them on Amazon. The three books set ( is something that's only available on our website. Our website is is a great place to start. We've got links out to all of the major retailers that are selling the books as well as a way for you to buy Autographed three book sets. I will compersonalize those autographs and send it out through our website. We have a ton of resources for parents, for teachers, for activities, for kids as well. We also have a girl CEO gallery with videos of 100 different girls between the ages of six and 16 who are running their own businesses. We're also always looking for more girls that we can profile. So if anyone is working with girl entrepreneurs, we would love to go to profile and you can just send it to our website for any resources. And of course, we're on social media @thestartupsquad and all the major platforms and always sharing information and tips about entrepreneurship and the girls that we work with.

Dr. Sonia Toledo: Awesome. We do have some girls that we introduced the idea of the profile and entrepreneurship website, so I'm really excited to have them join your team. I always believe that all the adults that are part of this movement, we are also deep learners and are constantly feeding ourselves with new information or some interesting information about what we do. Is there a book that you could refer to us so I could add to my book club on my website that you think would be great for our educators, parents, anyone who's engaged in the mindset of developing our young children?

Brian Weisfeld: I would love to recommend two books. One is good for educators and parents, and is more topical to entrepreneurship. It's called Venture Girls by Crystal Gong Cha. She runs a program called Venture Lab where they have a lot of entrepreneurship resources and programming. But it's a nonfiction book and it talks about the importance of the entrepreneurial mindset and integrating entrepreneurship education.

The other one, which I would like to recommend is a must read for parents especially. It’s called Rain Rain by Ann M. Martin, who wrote The Baby-Sitters Club. It has changed the way that I parent in that the character has neuro differences. Her father doesn't really understand her, but her uncle does. And it's just seeing how the father and the uncle interact with the girl in totally different ways really changed my perspective in terms of how I parent.

Dr. Sonia Toledo: That sounds priceless. That's probably definitely a pickup. It's been such an honor to talk to you and collaborate with you. We recommend our audience to check out The Startup Squad on our website. We are excited to partner as an affiliate with them. Have a look at their books, and this, for an individual parent, is great. Boys are also welcome to use these series of books because there's a lot of lessons in them. So it's not just for girls, it's for boys as well. Isn't that right Brian?

Brian Weisfeld: We describe ourselves as girl targeted, but boy inclusive. There's nothing anti boy about what we do, and almost all the speaking I do is to coed groups of boys and girls. But it was written with girls in mind and obviously has girl characters, but there's certainly no reason why boys don't enjoy it as much as girls do.

Dr. Sonia Toledo: It's great to talk to you.. Thank you.

Brian Weisfeld: And thank you for everything that you're doing for the kids as well, and for the educators out there that are inspiring our kids every day.


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